137848-28-3

Usage

Uses

Used in Asymmetric Synthesis:
(R)-NOBIN is used as a catalyst in the asymmetric phase-transfer catalysis (PTC) synthesis of α-amino acids. Its chiral nature allows for the selective formation of specific enantiomers, which is crucial in the production of biologically active compounds and pharmaceuticals.
Used in Polymer Science:
(R)-NOBIN is used as a reactant in the formation of poly(ester-amide)s when it reacts with trans-azobenzene-4,4′-dicarbonyl chloride. These polymers exhibit a backbone light-regulated chiroptical response, making them potentially useful in the development of advanced materials with applications in optics, sensors, and other technology-driven fields.
Used in Chemical Research:
Due to its unique structure and properties, (R)-NOBIN is also used in chemical research to study the effects of chirality on reaction mechanisms, catalysis, and the development of new synthetic methods. This contributes to the broader understanding of organic chemistry and the design of novel molecules with specific functions.
Used in Pharmaceutical Industry:
(R)-NOBIN's potential applications in the pharmaceutical industry are vast, as its chiral nature can be exploited to develop new drugs with improved efficacy and selectivity. The compound can be used in the synthesis of enantiomerically pure drug candidates, which is essential for ensuring the desired therapeutic effects and minimizing side effects.

Upstream product

• 91-59-8 naphthalen-2-ylamine 
• 135-19-3 β-naphthol 
• 134532-03-9 2-amino-2’-hydroxy-1,1’-binaphthyl 
• 18531-94-7 (R)-1,1'-Bi-2-naphthol 
• 425687-39-4 (+/-)-2-amino-2'-methoxy-1,1'-binaphthyl 
• 602-09-5 1,1'-bi-2-naphthol 
• 473699-18-2 (S)-(-)-2-(α-methylbenzylamino)naphthalene 
• 580-13-2 2-bromonaphthalene 

Downstream Products

• 137848-29-4 (S)-(-)-2'-amino-[1,1'-binaphthalene]-2-ol 

Relevant academic research and scientific papers

Tandem approach to NOBIN analogues from arylhydroxylamines and diaryliodonium salts: via [3,3]-sigmatropic rearrangement

Herein, we present a transition-metal free direct O-arylation of arylhydroxylamines employing diaryliodonium salts as arylation reagents to form transient N,O-diarylhydroxylamines that could subsequently undergo [3,3]-sigmatropic rearrangement and re-aromatization to afford structurally diverse NOBIN analogs in good to excellent yields under mild conditions.

Catalytic asymmetric synthesis of axially chiral 2-amino-1,1′-biaryl compounds by phase-transfer-catalyzed kinetic resolution and desymmetrization

An efficient methodology for kinetic resolution of axially chiral 2-amino-1,1′-biaryl compounds as useful chiral building blocks was developed by means of binaphthyl-modified chiral quaternary ammonium salt-catalyzed N-allylations under phase-transfer con

Synthesis and resolution of racemic 2-amino-2′-hydroxy-1,1′-binaphthyl

The title compound 3 has been prepared via a highly selective, Cu(II)-mediated cross-coupling of 2-aminonaphthalene 1 and 2-naphthol 2 and resolved into enantiomers via crystallization of diastereoisomeric salts with (1S)-(+)-10-camphorsulfonic acid. The method has been optimized and the use of chromatography eliminated.

Gram scale conversion of R-BINAM to R-NOBIN

A mild, operationally simple, and single-step transition-metal-free protocol for the synthesis of enantiomerically pure (R)-(+)-2′-amino-1,1′-binaphthalen-2-ol (R-NOBIN) from (R)-(+)-1,1′-binaphthyl-2,2′-diamine (R-BINAM) is reported. The one-pot conversion proceeds with good yield and shows no racemization. The hydroxyl on the R-NOBIN product was shown to have come from water in the reaction medium via an H218O study. The correct value of the specific rotation of R-NOBIN was reported.

Stereoselective Synthesis of Optically Pure 2-Amino-2′-hydroxy-1,1′-binaphthyls

Direct entry to optically pure 2-amino-2′-hydroxy-1,1′-binaphthyl (NOBIN) derivatives by an iron-catalyzed stereoselective oxidative cross-coupling reaction between 2-naphthol and 2-aminonaphthalene with a labile chiral auxiliary is reported. This efficient method offers entry to tailor-designed (Ra)- and (Sa)-NOBINs that are not accessible by any other means.

Kinetic resolution of axially chiral 2-amino-1,1′-biaryls by phase-transfer-catalyzed N-allylation

Going through a phase: The highly selective kinetic resolution of the title compounds, which are important chiral building blocks, was achieved by phase-transfer-catalyzed N-allylation. This synthetic method was applied to the highly enantioselective desymmetrization of a biaryl compound. Copyright

Switchable Smiles Rearrangement for Enantioselective O-Aryl Amination

Asymmetric assembly of atropisomeric anilines from abundant and readily available precursors is one of the most challenging but valuable processes in organic synthesis. The use of highly efficient Smiles rearrangement to accomplish switchable enantioselec

Kinetic resolution of 1,1-biaryl-2,2-diols and amino alcohols through NHC-catalyzed atroposelective acylation

We present here a highly efficient NHC-catalyzed kinetic resolution of a wide range of 1,1-biaryl-2,2-diols and amino alcohols to provide them in uniformly ≥99% ee. This represents the first highly enantioselective catalytic acylation of axially chiral alcohols. The aldehyde backbone that is incorporated into the chiral acyl azolium intermediate was found to have a significant effect on the enantioselectivity of the process.

A Chiral Iron Disulfonate Catalyst for the Enantioselective Synthesis of 2-Amino-2′-hydroxy-1,1′-binaphthyls (NOBINs)

A novel type of chiral redox disulfonate iron complex for asymmetric catalysis is reported. The [Fe((Ra)-BINSate)]+(BINSate = 1,1′-binaphthalene-2,2′-disulfonate) complex effectively promotes the enantioselective oxidative cross-coupling between 2-naphthols (1) and 2-aminonaphthalene derivatives (2), affording optically enriched (Ra)-2-amino-2′-hydroxy-1,1′-binaphthyls (NOBINs) with exceptional yields and enantioselective ratios (up to 99% yield and 96:4 er). The [Fe((Ra)-BINSate)]+catalyst was designed as a chiral version of FeCl3with multicoordination sites available for binding the two coupling partners 1 and 2 as well as the oxidant. Our structure-selectivity and activity study, which covered most of the important positions in the NOBIN scaffold, revealed the effect of different substitution patterns on the coupling efficiency and stereoselectivity.

Synthesis and application of N-3,5-dinitrobenzoyl and C3 symmetric diastereomeric chiral stationary phases

Three diastereomeric chiral compounds, namely, (R,R)-(+)-2-amino-1,2-diphenylethanol, (1S,2R)-(+)-2-amino-1,2-diphenylethanol, and (1R,2R)-(+)-1,2-diphenylethylenediamine were used as starting materials for preparing three N-3,5-dinitrobenzoyl derivative